57443-39-7Relevant academic research and scientific papers
Iron-Catalyzed Cross-Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols
B?ckvall, Jan-E.,Bermejo-López, Aitor,Posevins, Daniels
supporting information, p. 22178 - 22183 (2021/09/06)
Herein we disclose an iron-catalyzed cross-coupling reaction of propargyl ethers with Grignard reagents. The reaction was demonstrated to be stereospecific and allows for a facile preparation of optically active allenes via efficient chirality transfer. Various tri- and tetrasubstituted fluoroalkyl allenes can be obtained in good to excellent yields. In addition, an iron-catalyzed cross-coupling of Grignard reagents with α-alkynyl oxetanes and tetrahydrofurans is disclosed herein, which constitutes a straightforward approach towards fully substituted β- or γ-allenols, respectively.
Chiral Bifunctional Phosphine Ligand Enabling Gold-Catalyzed Asymmetric Isomerization of Alkyne to Allene and Asymmetric Synthesis of 2,5-Dihydrofuran
Cheng, Xinpeng,Wang, Zhixun,Quintanilla, Carlos D.,Zhang, Liming
supporting information, p. 3787 - 3791 (2019/03/07)
The asymmetric isomerization of alkyne to allene is the most efficient and the completely atom-economic approach to this class of versatile axial chiral structure. However, the state-of-the-art is limited to tert-butyl alk-3-ynoate substrates that possess
DBU-promoted carbonylative synthesis of 1,3-oxathiolan-2-ones from propargylic alcohols with TFBen as the CO source
Ying, Jun,Zhou, Chao,Wu, Xiao-Feng
supporting information, p. 1065 - 1067 (2018/02/22)
A DBU-promoted carbonylative cyclization of propargylic alcohols with sulfur was developed. Various 1,3-oxathiolan-2-ones were produced in 61-98% yields under mild conditions in the absence of metal catalysts. TFBen (benzene-1,3,5-triyl triformate) as an efficient and solid CO surrogate and S8 as an ideal sulfur source were employed and incorporated.
Synthesis and Utility of 2,2-Dimethyl-2 H-pyrans: Dienes for Sequential Diels-Alder/Retro-Diels-Alder Reactions
Tejedor, David,Díaz-Díaz, Abián,Diana-Rivero, Raquel,Delgado-Hernández, Samuel,García-Tellado, Fernando
supporting information, p. 7987 - 7992 (2019/01/04)
The practical use of 2,2-dimethyl-2H-pyrans as electron-rich dienes in sequential Diels-Alder/retro-Diels-Alder (DA/rDA) domino processes to generate aromatic platforms has been demonstrated. Different polysubstituted alkyl 2-naphthoates have been synthesized by the DA/rDA reaction of benzynes and 2,2-dimethyl-2H-pyrans. The use of other activated alkynes allows the access of substituted alkyl benzoate derivatives.
A Method for the Late-Stage Formation of Ketones, Acyloins, and Aldols from Alkenylstannanes: Application to the Total Synthesis of Paecilonic Acid A
Sommer, Heiko,Hamilton, James Y.,Fürstner, Alois
supporting information, p. 6161 - 6165 (2017/05/22)
Treatment of alkenylstannanes with Cu(OAc)2/Et3N affords the corresponding enol esters or ketones under conditions that proved compatible with many common functionalities; these include groups that would neither survive under the sta
Synthesis of Oxazolidin-2-ones by Tandem Cyclization of Propargylic Alcohols and Phenyl Isocyanate Promoted by Silver Catalysts as π-Lewis Acids
Sekine, Kohei,Mawatari, Takanori,Yamada, Tohru
supporting information, p. 2447 - 2450 (2015/10/19)
Highly Z-selective syntheses of oxazolidin-2-ones from propargylic alcohols containing internal alkynes and phenyl isocyanate were achieved by using a combination of silver acetate and N,N-dimethylaminopyridine. The catalytic system was applied to proparg
Rh(I)-catalyzed allenic Pauson-Khand reaction: First construction of the bicyclo[6.3.0]undecadienone ring system
Mukai, Chisato,Hirose, Toshiyuki,Teramoto, Satoshi,Kitagaki, Shinji
, p. 10983 - 10994 (2007/10/03)
The Rh(I)-catalyzed Pauson-Khand reaction of allenynes afforded the bicyclo[6.3.0]undecadienones as well as their benzo and furo derivatives. In addition, a novel [RhCl(CO)2]2-catalyzed [2,3]-sigmatropic rearrangement of the sulfinic
